10 of Our Favorite Free Spirits

A good friend of mine has spent the better part of the past year living out of a backpack filled with not much more than a few changes of clothes, her laptop, and whatever withered paperback she’s reading that week. Whether in France, Croatia, or Thailand, she’s quick to adapt, always making new friends along the way. Maybe you have a friend like this, too—an adventurer who bucks convention and lives by their own rules. In honor of our Freewheeling theme for May, we celebrate ten famous open-minded ladies who’ve carried that untethered torch throughout history, decade by decade.

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1920s: Clara Bow

Few people embodied the devil-may-care flapper attitude of the Roaring Twenties quite like this silent film actress, who made a name for herself with her mischievous screen presence. Flaunting pencil-thin arches and a flirty bob, Bow defined quirky femininity—all with a knowing wink—in films like It (which spawned the term “it-girl”) and Mantrap.

Photo: Getty Images

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1930s: Amelia Earhart

Up until her mysterious disappearance in 1937, this airborne trailblazer made history as the first female pilot to cross the Atlantic ocean solo, and the first person (man or woman) to fly alone from Honolulu to Oakland, California. Earhart bucked gender roles, inspiring women everywhere to do whatever they want to do—conventions be damned.

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1940s: Katherine Hepburn

Sporty and whip-smart, Katherine Hepburn paved the way for Hollywood’s modern woman. Known for screwball comedies like Bringing up Baby and The Philadelphia Story, Hepburn proved that leading ladies could be both beautiful and clever—unfortunately a fairly novel idea at the time.

Photo: Getty Images

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1950s: Bettie Page

Through her tongue-in-cheek modeling gigs (and her trademark bangs) Page was ahead of her time, unafraid to flaunt her sexuality in unprecedented and empowering ways. She built a career that lasted almost a decade as the “Queen of Pin-Ups.”

Photo: Getty Images

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1960s: Nina Simone

The songwriter otherwise known as the “High Priestess of Soul” used her one-of-a-kind voice to bring attention to the civil rights moment. With recordings like “Four Women” and “Strange Fruit” (which may sound familiar to Kanye fans) Simone made waves onstage (and off) for change.

Photo: Philips

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1970s: Patti Smith

Following the herd was never an option for Smith. In just a few years after moving to New York, this musician/poet/writer became the godmother of the city’s male-dominated downtown punk scene and muse to photographer Robert Mapplethorpe. She lived to tell the tale, which you can read in her soulful memoir, Just Kids.

Photo: Ecco

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1980s: Madonna

After breaking out of the ‘80s dance hall scene, Madge blew minds with her envelope-pushing performance of “Like a Virgin” at the 1984 MTV Video Music Awards. Since then she’s made her name as a pop star unafraid of speaking her mind—even when it means upsetting her corporate sponsors.

Photo: Getty Images

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1990s: Drew Barrymore

Few actresses celebrated the ‘90s flower child revival quite like Barrymore, who was known to show up on a red carpet with daisies in her hair and stars in her eyes. Though her hippie ways have been mocked everywhere from SNL to Mean Girls, we’ve always admired Barrymore’s ability to wear her heart on her sleeve.

Photo: Getty Images

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2000s: Gwen Stefani

In an era of bubblegum pop stars Britney and Christina, Gwen Stefani stayed her singular course with No Doubt, recording songs that explored themes of independence, marriage, and motherhood. She reminded us that radio pop could also be pensive—and pink hair was infinitely cooler than blonde extensions.

Photo: Getty Images

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2010s: Janelle Monáe

With her signature tuxedo and pompadour, this genre-blurring performer has made a name for herself as arguably the decade's most original pop star by combining the sounds of R&B, doo-wop, classic soul, and pop music. With her frequent futuristic, sci-fi references (she has said she "only dates androids”), she’s a bona fide twenty-first century free spirit.

Photo: Getty Images

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